Looking Sideways

Looking Sideways

Insights

Insights: 5 Creative Lessons From Oscar-Winning Director Orlando von Einsiedel

“You’re always starting again. In a way, each film asks you to figure it out from the beginning.”

Mar 25, 2026
∙ Paid

One of my absolute favourite things about hosting Looking Sideways is when a conversation reaffirms fundamental truths about the realities of the creative life.

Think of my ongoing exchanges with artist Thomas Campbell about how years of patient, thoughtful creative endeavour led him to his opus Yi-Wo:

Episode 251: Thomas Campbell - Yi-Wo

Episode 251: Thomas Campbell - Yi-Wo

Matthew Barr
·
September 30, 2025
Read full story

Or last year’s chat with director Lucy Walker about how she developed the multi-award-winning Mountain Queen:

Episode 248: Lucy Walker - Ways of Seeing

Episode 248: Lucy Walker - Ways of Seeing

Matthew Barr
·
April 29, 2025
Read full story

Then there’s my discussion with Adam Skolnick about his decades-long quest to bring his recent novel American Tiger to life:

Episode 254: Adam Skolnick - Fellow Traveller

Episode 254: Adam Skolnick - Fellow Traveller

Matthew Barr
·
December 10, 2025
Read full story

And that’s just in the last year.


To this list, you can add my recent live Kendal Mountain Festival conversation with Oscar-winning filmmaker Orlando von Einsiedel.

On paper, Orlando’s remarkable career represents the summit of modern documentary filmmaking.

With Virunga, The White Helmets, The Lost Children, and his forthcoming The Cycle of Love, Orlando’s films have shaped the visual and emotional language of contemporary non-fiction storytelling in ways that will resonate for years.


And from the outside, this looks like the creative promised land. Surely Orlando is now in a position to name his price and call his own creative shots?

What emerged from our conversation, instead, was yet another pitiless reminder of what it actually takes to sustain a creative career. Even when you’ve got an Oscar on the CV.

Here are my key creative lessons from this vital conversation…


Insights is the Looking Sideways section, exclusively for my paid subscribing community.

It’s an absolute treasure trove of the - well - insights and wisdom imparted by over 250 Looking Sideways guests; as well as from the 25 plus years I’ve been making a living as a journalist, author, podcaster, business owner, mentor and speaker.

It’s where you’ll find exclusive blogs, podcasts, video chats, guest posts and articles all geared towards answering that two fundamental questions:

  • How can I spend more time doing the things I’m passionate about?

  • What does a ‘successful’ creative life actually look like?

Here are a few recent Insights articles to whet your appetite:

Insights: How Filmmakers REALLY Make Money - Part 1

Insights: How Filmmakers REALLY Make Money - Part 1

November 5, 2025
Read full story
Insights: 5 Things I've Learned - Db CMO Jon Weaver

Insights: 5 Things I've Learned - Db CMO Jon Weaver

September 23, 2025
Read full story
Insights: What I've Learned Running My Company All Conditions Media - Redux

Insights: What I've Learned Running My Company All Conditions Media - Redux

Matthew Barr
·
July 6, 2025
Read full story
Insights: What I’ve Learned About Being A Freelancer - Part 1

Insights: What I’ve Learned About Being A Freelancer - Part 1

Matthew Barr
·
March 11, 2022
Read full story
Insights: 5 Things I've Learned - Finisterre CMO Bronwen Foster-Butler

Insights: 5 Things I've Learned - Finisterre CMO Bronwen Foster-Butler

Jan 11
Read full story

Get access by subscribing below…


1. Creative careers are never secure - even if you’ve won an Oscar

The simple, sobering reality that uncertainty never disappears, no matter what level of ‘success’ you attain, was perhaps the most important lesson of the entire conversation.

User's avatar

Continue reading this post for free, courtesy of Matthew Barr.

Or purchase a paid subscription.
© 2026 Matthew Barr · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture